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Org Lett. 2017 Jul 07;19(13):3672-3675. doi: 10.1021/acs.orglett.7b01719. Epub 2017 Jun 21.

Sequential Catalysis of Phosphine Oxide for Stereoselective Synthesis of Stereopentads.

Organic letters

Shunsuke Kotani, Kosuke Kai, Masaharu Sugiura, Makoto Nakajima

Affiliations

  1. Graduate School of Pharmaceutical Sciences, Kumamoto University , 5-1 Oe-honmachi, Chuo-ku, Kumamoto 862-0973, Japan.
  2. Priority Organization for Innovation and Excellence, Kumamoto University , 5-1 Oe-honmachi, Chuo-ku, Kumamoto 862-0973, Japan.

PMID: 28636385 DOI: 10.1021/acs.orglett.7b01719

Abstract

An efficient method for accessing enantiomerically pure stereopentads via a catalytic asymmetric sequential aldol reaction has been developed for the first time. The enantioselective sequential aldol reaction produces a wide range of chiral stereopentad precursors in good yields with excellent enantioselectivities. The key to success is the use of the sequential catalytic system involving a chiral phosphine oxide catalyst and trichlorosilyl triflate.

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